Chipmunk Politics
by Somnion
Summary: Alvin and Brittany are tied for the election of school president and once again, Jeanette has the deciding vote. Not willing to accept defeat, Alvin enlists the aid of his brother Simon to 'encourage' Jeanette to make the 'right' vote. All usual pairings
1. The Plan is Hatched

Title: Chipmunk Politics

Written by: Somnion

Disclaimer: I do not own Alvin and the Chipmunks. They belong to Bagdasarian Productions

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Chapter One: The Plan is Hatched

Alvin paced to and fro in his room. Things were obviously not going according to plan, he thought to himself. Theodore was busy working on an election poster but had noticed his elder brother's distress and it bothered him greatly. The election for school president was going on and both Alvin and his counterpart Chipette, Brittany, had enlisted as candidates. It was really becoming a problem; both were highly competitive and charismatic, promising a very tough election on both sides. Theodore was getting worried for Alvin; his outgoing older sibling was never the kind of person who'd accept defeat and losing to Brittany would have been even harder for him to accept because not only would he have to face the humiliation of losing but he would also, although he'd never admit it, have to risk losing favour in the eyes of the auburn haired Chipette. Both Chipmunks turned their attention to the sound of an opening door, its gentle scraping against the carpeted floor pulling them away from their individual thoughts. Their tall, bespectacled brother, Simon stood in the doorway, his hand holding a file and Alvin was well aware of the contents.

"What's the situation looking like, Simon?" Alvin asked half-heartedly.

The tallest Chipmunk shook his head, and Alvin began to brace himself for whatever news that Simon had brought with him. "It's not good," was Simon's simple reply.

"Give it to me straight, Simon," Alvin asked in response. "What's the polls looking like?"

"It's Déjà Vu, Alvin," Simon said with a sigh. "You and Brittany are tied once again, with only one vote uncounted for. I'm sure you know whose it is..."

"Jeanette's vote, huh?"

Simon nodded his head in acknowledgement. It really was a replay of the year before where both Brittany and Alvin had run for school president; both of them were tied and Jeanette, just as this year, had the deciding vote. However, Brittany had just transferred to their school that year and didn't have any knowledge of the issues concerning the school and was running simply as a way to increase her popularity and Jeanette, feeling that her older sister was running for the wrong reasons, voted for Alvin instead for her sister. Alvin didn't have that advantage this time around; Brittany was just as up to date on all the issues of the school as Alvin was, giving Jeanette no reason to vote for Alvin over her sister.

"We're sunk," Alvin said sorrowfully. "Jeanette's sure to vote for her sister this time."

"Yea, it sure looks that way," agreed Simon as pushed his glasses up.

"At least you gave it your best shot, Alvin," assured Theodore as he walked over to his upset brother and patted his back to comfort him.

"With Brittany completely up to date with all the issues and her preparations, I've definitely got no way to get Jeanette's vote," complained Alvin.

"You've lost the advantage you had before, Alvin," said Simon sympathetically. "We may as well accept the defeat graciously."

Alvin, despite his pride, was wiling to do that but just then he noticed something in Simon's hand, a small book with a pastel purple colour. It was odd, to say the least, so he questioned his logical brother about the little book he held.

"Oh, it's a book of poems that Jeanette lent me," answered Simon as he passed Alvin the book. "She says the style of poetry is very profound and she thought I might be interested in taking a look."

Alvin looked over the book Simon had handed him. Seemed a little feminine from his first glance and as he quickly glanced over the pages he understood why; the book was a collection of love poems. Knowing Simon, he would have thought that Jeanette had lent him the book so that he could inspect the style of the writing and poetry but Alvin knew that Jeanette had given him that book for another reason. Alvin knew that Jeanette had always watched Simon and that this book was her way of silently reaching out to him, a way with which she could convey her feelings without actually saying them. Suddenly, it occurred to him that although he had lost one advantage, he still had another ace up his sleeve. Jeanette was in love with Simon and he could very well use that bond to his advantage. All that was needed was to push Simon in the right direction, using Simon as a means to get Jeanette to vote for him over Brittany, after all, Simon and Jeanette would be happy together and he'd be happy when he'd get Jeanette's vote, so in the end, everyone would be happy with the obvious exception of Brittany who would lose the election. The idea seemed so ingenious that he almost slapped his forehead over his foolishness of not thinking about it before.

"I know that smile, Alvin," Simon said with a frown as he noted the mischievous smile that was smeared across his brother's lips. "Whatever it is, forget about it."

"We may not have lost after all, Simon," he said gleefully. "We still have one last advantage."

"And what pray tell might that be?" asked Simon sarcastically.

"You," Alvin answered as he returned Jeanette's book to Simon.

"I don't like where this is going, Alvin."

"Listen," Alvin said calmly as he put his arm over his brother's shoulders, "you're close with Jeanette, right? So, you're the only one who can push her in the right direction, the direction to my winning vote."

"That's dirty politics, Alvin," Simon said with a tone of displeasure. "That's almost as if you're using me to seduce her into voting for you. It's just wrong."

"Please, Simon. I need to win this election," pleaded Alvin as he got on the floor, grabbing Simon's foot while grovelling and begging the whole time.

"Why, Alvin?" asked Simon impatiently. "Give me one good reason why I should help you do this."

Another smile came upon Alvin's face as he looked up and judging from the smile, Simon knew that he should brace himself for something unexpected.

"It would be a shame if Dave found out who was responsible for the colony of termites that was nesting in the garage, Simon."

Simon gulped fearfully. "You wouldn't..."

"So, you'll help me out then, Simon?" Alvin asked with a triumphant smile as he got up and extended his hand towards the blue-clad Chipmunk.

Simon sighed as he shook his brother's hand, sealing the agreement. He knew he'd regret this before the election was over but for now, he'd pray and hope that things might turn out for the better.

Chapter One Ends

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A little bland but this is just to set the stage for the story, the real exciting bits shall come soon. As always, I look forward to your words, suggestions and opinions so please send me a review and tell me what you think.


	2. The First Step of Deception

Title: Chipmunk Politics

Written by: Somnion

Disclaimer: I do not own Alvin and the Chipmunks. They belong to Bagdasarian Productions

Sorry for the delayed update, final examinations coming around so I'm a little busy juggling studies and computer games (just bought Strong Bad's Cool Game for Attractive People). As many of you have probably realized, this story is based on the episode 'May the Best Chipmunk Win'. In fact the events of that episode are supposed to have happened the year before in this story, so I'm not stealing the idea, just playing off the idea (I don't want to infringe any copyright laws and get sued). Well, here's the next chapter, I'll try to update as soon as I can and I hope you guys will find this chapter enjoyable.

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Chapter 2: The First Step of the Deception

"This is a miserable idea, Alvin," Simon said as he and his brothers stood outside the florist shop.

"Well, you can't very well charm Jeanette without flowers," Alvin explained as he pulled his reluctant brother into the florist.

The florist shop was an explosion of colours, flowers of every shape and size could be found. It was a beautiful sight and Simon had half a mind on dropping the whole idea of actually buying anything and start examining and categorizing the flowers. As he took in the sights and scents of the wonderful flora that surrounded him, Alvin came up to him holding a large bouquet of roses.

"You can never go wrong with these roses," he said with a grin.

"Alvin, aren't roses a bit too direct. I do not want to make it seem like I'm going to ask Jeanette to marry me."

"Come on, Simon, everyone loves roses. You think so too, don't you, Theodore?" asked Alvin defensively.

"I agree with Simon, Alvin. I mean it is Jeanette that Simon's buying them for. I think the flowers should be a little more unique to show that she's special," Theodore said thoughtfully.

"Great idea, Theodore," commented Alvin, once Theodore had given his suggestion.

Theodore sighed for he didn't like this idea at all. However, Alvin was very determined to win and with Simon being blackmailed he felt that helping his intelligent older brother might somehow show the mischievous Alvin how wrong this trick was. Furthermore, he knew that Simon would have felt very guilty doing this so he didn't want him to feel as though he were alone; for that reason, Theodore was willing to share the guilt with his brother.

"Is there something I can do for you, boys?" asked a young woman who had approached them, a woman who the Chipmunks recognized was the florist.

"My brother is looking for a special bouquet of flowers for a special girl," Alvin answered with a smile, pointing in Simon's direction.

""Well, that's nice," replied the florist. "Are you two here to help him pick out flowers? You're such nice brothers. Perhaps I can help?"

"Really?" asked Alvin in earnest.

"Do you boys know that flowers can convey secret meanings?" questioned the woman.

When all three Chipmunks shook their heads, she explained, "Depending on what flowers you present to someone, it will allow you to say a subtle message to the recipient of the flowers. For example, Baby's breath means happiness and pink heather bouquets usually are to wish people good luck. Why don't you tell me a little about this girl you wish to send these flowers to?"

"Well," Simon answered awkwardly, "she's quite quiet, a bit shy but she's a very nice person."

After a minute of thinking, the florist exclaimed that she had found the right bouquet for Simon. She picked some white carnations, a few white hibiscuses gathering them in a bouquet and in finality, complementing the flowers with a lace of yellow jasmines. The three boys were all speechless when they beheld the completed bouquet, it was absolutely beautiful.

"What does it mean?" asked Simon, for he was eager to find out what the message hidden in the flowers was.

"White carnations mean innocence or pure love, hibiscus stands for delicate beauty and the yellow jasmines depict timidity and modesty," replied the florist.

"This is perfect," Alvin exclaimed in delight. "That's just the kind of bouquet you need for Jeanette."

"Alvin, I..."

Alvin, upon realising his brother's conscience turn, quickly paid for the flowers and dragged his two siblings out. He couldn't afford Simon getting noble at a time like this, there was just too much at stake.

"Alright," announced the cheeky Chipmunk as they walked down the street, "we've got the flowers. All we have to do now is send them."

As Alvin proceeded to carry out the plan, Simon and Theodore followed behind, both wallowing in guilt and dearly hoping that Alvin would come to his senses.

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Today was a pleasant day at the Miller's residence; well at least it was for Jeanette. When Brittany had become aware that her timid little sister had the deciding vote, she was pulling out all the stops to make sure she was exceptionally nice to Jeanette. Brittany had even gone out of her way to help Jeanette with her chores. The day couldn't get any better, Jeanette thought to herself as she dug into a nice novel while sitting on the sofa. Suddenly, there was a ring of the doorbell.

"I wonder who could that be?" Jeanette wondered as she opened the door.

Strangely there was no one to be seen, the only thing present was a very beautiful flower bouquet with a card left on the welcome mat. 'Wouldn't it be nice if these were for me', she thought to herself. However, all the bouquets of flowers that were being left on their doorstep were for Brittany and her election. However, when Jeanette picked it up, she was astonished when she saw that it was not Brittany's name but her own name that was written on the card. What surprised here even more was that she recognized the handwriting on the card and that it was Simon's hand.

"More flowers?" Brittany asked from across the hall; she too had heard the bell and was on her way to answer the door.

Jeanette, however, was too stunned to reply. She was still in the process of trying to register the fact that she had received the most beautiful bouquet of flowers she had ever seen from Simon. Furthermore, Jeanette was well aware of the meanings of those flowers for she had read it up in a book before. Did Simon really think of her as the hidden message the flowers suggested? As Jeanette continued to ponder on the subject, Brittany continued to call out to her sister but when the bespectacled Chipette failed to reply, Brittany, who was obviously upset for being ignored, came up to her angrily.

"JEANETTE! Are you listening to me? I asked you a question."

"Oh...sorry, Brittany," apologized Jeanette as she finally came to herself.

"Honestly, Jeanette. I must have called you six times and you still didn't answer. What's so interesting here anyway?"

"Well...this bouquet came for me and it's from Simon, and..."

When Brittany heard that her sister had received a bouquet of flowers from Simon, she immediately jumped to the conclusion that Alvin had put Simon up to help him in winning Jeanette's vote. Brittany knew Alvin better than any of the Chipettes and she was well aware of what he was capable of. Were it any other time than this, she would have dismissed the flowers as a sweet gesture from the logical Chipmunk to her sister but the election had induced a temporary state of paranoia in the auburn haired Chipette.

"I can't believe Simon would sink so low," she said in disgust. "Trying to charm you with flowers so you would vote for Alvin."

"Are you sure, Brittany?" asked Jeanette softly. "Maybe he really..."

"Oh, don't be so naive, Jeanette," interrupted Brittany. "It's obvious he's working with his brother because he wants Alvin to win and for me to lose the election."

Brittany would have continued in her crusade to demonise the Chipmunks as manipulative weasels had it not have been for Miss Miller interrupting the quarrel. She had overheard the commotion and given where the direction of the conversation was heading to, she believed it was due time she stepped in.

"Now, now Brittany, settle down," she said as she tried to calm the agitated Chipette.

"But, Alvin is trying to use Simon to manipulate Jeanette," argued Brittany in her defence. Miss Miller let out a sigh before continuing to speak.

"I know Alvin can be a mischievous one and bit childish when it comes to winning but he has a kind heart so I doubt he would do something so terrible," she replied. "Furthermore, Simon is a very trustworthy boy and I doubt that he would even consider such a deception."

With that she told the two girls to stop bickering about the flowers and to go wash their faces before they came down to dinner. Jeanette went to put the flowers in some water while Brittany went upstairs to wash her face. Although Miss Miller had told her otherwise, she still couldn't shake off the feeling that the Chipmunks had an ulterior motive in this affair.

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"I'm telling you, Eleanor, I know Alvin and Simon are up to something," argued Brittany after dinner.

Eleanor looked up from her homework which was laid out on her bed. "Brittany, please don't jump to conclusions. I don't think Alvin and definitely not Simon, could be that mean."

"Oh, is that so, Eleanor?" Brittany retorted in annoyance, "Don't forget that this is Alvin we're talking about. Do you remember that time he was crushing on Miss Stone but Dave started dating her instead? He went so far as to sabotage Dave's date with her."

"Well, that's true but Simon..."

"Oh, don't think that Simon is such an angel. Don't forget that time he tricked his entire family into wearing that thinking cap so that they could cheat on that nerd game show he always watches. You have to admit Eleanor, that's the type of thing Alvin would usually do."

"I guess," admitted Eleanor.

"The acorn can't fall too far away from the tree, Eleanor. I wouldn't be too surprised if 'sweet, innocent Theodore' isn't involved in this as well."

Brittany still had more arguments to bring to the table but both she and Eleanor were startled by a loud sound coming from the bathroom. They rushed down to the bathroom and were surprised when they found the bathroom in a mess with Jeanette in the middle of it wearing some very badly applied makeup on her face and her makeup kit thrown all over the bathroom floor. The two Chipettes looked in confused astonishment as Jeanette tried to explain the situation to them.

"I'm...I'm not playing with makeup. This...is a science experiment," blurted the brown haired Chipette.

Brittany raised an eyebrow in disbelief, a clear sign saying 'Do you really think we believe that, Jeanette?'

"I can explain the lipstick..."

"What's going on, Jeanette?" asked Brittany bluntly as she grabbed a towel to help clean up the makeup on Jeanette's face.

"Well..."

"Com on, Jeanette," asked Eleanor comfortingly as she went over and held her sister supportively. "Tell us what's going on. We're your sisters after all."

"Well, in that card that came with the bouquet," Jeanette replied softly, "Simon asked if I would like to go to visit the city aquarium with him tomorrow and I called him and said yes."

"YOU DID WHAT?!" yelled Brittany in shock and anger. "Jeanette, he's just using you. He and Alvin are obviously trying to deceive you to vote for Alvin in the election."

"We don't know that for sure, Brittany," argued Eleanor, taking the Chipmunk's side once again.

Brittany still believed that the Chipmunks were planning some kind of deception, she was very set in her ways and could be extremely stubborn, and she was about to continue the argument, only to be interrupted by Jeanette.

"I know it's possible that they could be doing that, Brittany," she said to her elder sister. Hearing Jeanette take her side, Brittany's temper simmered down.

"But the Chipmunks are our friends," she continued, "and that means that we should trust them. It's not me just believing in Simon's honesty but in Alvin's and Theodore's too."

Both Chipettes looked at their sister, neither saying a word. After a while, Brittany took Jeanette's hand and lifted her up.

"Come on, Jeanette. We have to get going," she said to the green eyed Chipette.

"Get going? Going where?" asked Jeanette in confusion.

"Well, you do have a date tomorrow, Jeanette," Brittany said with a smile. "And there is no way I'm going to let you go on your first date looking like this."

Chapter 2 Ends

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As always your reviews and opinions are greatly appreciated.


	3. The Date: Part One

Title: Chipmunk Politics

Written by: Somnion

Disclaimer: I do not own Alvin and the Chipmunks. They belong to Bagdasarian Productions

Sorry for the late update guys. First of all, I want to thank all the readers for their patience for bearing with me, I'm really sorry for being tardy with the updates. I also want to thank those who reviewed, I'm very grateful you guys took the time to write. The reason for the late update for this chapter is because I tried really hard to make the characters stay in character and I also wanted to set the stage for possible side pairings for Alvin and Brittany as well as Theodore and Eleanor. That said, the Simon and Jeanette date chapter, which I had originally intended to be a single chapter will be extended to two chapters, this chapter being the first of the two. Anyway, I hope you guys will enjoy this and I'll try to update as soon as I can for my stories.

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Chapter 3: The Date: Part One

Simon sat on the bench as he read a book in the Saturday morning sun. He'd been waiting at the meeting place earlier than he usually would, an hour earlier in fact, due to his nervousness. As he waited for the brown haired Chipette whom he would be touring the aquarium with, Simon scratched the back of his ear, not out of boredom, but because the wire, the one that had Alvin insisted he wear so that the red clad Chipmunk could relay instructions to him so he could effectively court Jeanette and in finality, convince her and get her to vote for Alvin, itched and it annoyed the bespectacled Chipmunk.

"Stop picking at it, Simon," yelled Alvin's voice over the wire. "You're going to loosen it."

"Can I help it if it itches, Alvin?" snapped Simon sarcastically.

"It has to be lodged in perfectly, Simon. We can't afford any risks here," stated Alvin impatiently. "So stop picking at it, Simon."

Choosing to ignore Alvin's complaints about his picking on the wire, Simon returned back to reading the little book he had brought with him. Occasionally, he would draw his attention away from the book and survey his surroundings, looking for any sign of the Chipette he was supposed to meet today. As every minute passed, his anxiety built up steadily and he found himself gulping silently to help keep his composure. He tried to focus on something else, looking around as he watched the birds that sat in the trees. He smiled to himself when he noticed a Belted Kingfisher perched on a branch overlooking the pond. Alvin noticed his nerdy brother's jitteriness and figured he better say something to calm him down.

"Quit worrying, Simon. It's just Jeanette," Alvin assured over the wire.

Alvin would have continued assuring Simon but just then, Alvin found his attention being diverted to a pretty girl walking around, as though she was lost. Alvin smiled as he told Theodore, who was hiding with him behind the bushes with him, to cover for him for a minute. Putting on his most charming smile, he waltzed up to the lost girl.

"Pardon me, Miss," he said suavely, "You seem lost. May I help you?"

"Yes, actually," said the girl as she turned to the Chipmunk's direction. "I'm looking for a friend of mine named…ALVIN?!"

To say Alvin was shocked was understatement; he was flabbergasted. The girl he was just about to sweet talk was his brother's missing date, Jeanette. Of course, she didn't look like Jeanette at first, she looked far too well dressed and Alvin knew that it was probably Brittany who had dolled up her little sister for the date.

'Jeanette!" Alvin said in surprise. "I didn't recognize you. Wh...What are you doing here?"

Alvin knew full well why she was here, but if Jeanette knew that Alvin knew she had a date with Simon, she might have started getting suspicious.

"Actually, I'm meeting, Simon," she said shyly.

"On a date?" Alvin asked mischievously, still feigning ignorance.

"Yes…"

"Well, you better hop to it, wouldn't want to keep your Simon waiting," replied Alvin, doing his best to remain as cheeky as possible so as to avoid any suspicion.

"Of course. I'll see you later, Alvin," answered Jeanette as she rushed off to find her date.

Alvin took in a deep breath as he watched Jeanette walk away; this was an unexpected turn of events. Given how nice Jeanette looked, Simon was going to have a hard time keeping his head on his shoulders. Slowly, Alvin pressed the button on the wire attached to his ear, relaying his message to his brother.

"Simon, I just met, Jeanette, she's on your way now."

"Roger, I hear you, Alvin," replied Simon on the other line.

"Oh, and Simon, scratch what I just said earlier about worrying. Start worrying."

Simon didn't understand what Alvin meant but he couldn't really ask him because he then heard a soft voice call from behind him.

"Hello, Simon," called the voice, which Simon recognized was Jeanette's.

"Hello, Jeanette," greeted Simon in reply as he turned around.

Turning around, then Simon realized just what Alvin had meant. The girl he saw standing in front of him was definitely Jeanette yet at the same time she looked so different. His expression must have shown, because Jeanette began to blush suddenly as she started to explain.

"The...outfit was...Brittany's idea," Jeanette said shyly, her fingers fidgeting with one another. "She...insisted I needed a make-over."

Simon had to admit, although Brittany was an average student academically, when it came to fashion and style, the pony tailed Chipette was a genius, even more so than Alvin was, and the way she had dressed Jeanette up was proof of that. Jeanette had never looked so pretty. She had traded her usual blue turtleneck for a much more fitting one, and although the new one was still roomy, it gave her a look of intelligence about her rather that of sloppiness which her old one had given. She wore a long purple skirt that cut off a few inches below her knees instead of her usual short pleated one. She wore new red sneakers, ones that fit her foot size and fitting socks that didn't dangle at her ankles as her old ones did. Her makeup was brilliantly done for although she wore very little of it and was simple, just a little bit of blush, peach coloured lipstick and light purple eye shadow, it was enough to highlight her pretty features. Finally, he saw that she had changed the way she kept her hair and wore it in a French braid and held at the end with a lavender coloured ribbon tied up in a bow. Her spectacles were the only thing that had not changed about her, which was a good thing because if she had taken them off, she'd be bumping into every lamp post and mailbox in the neighbourhood.

Alvin may have been able to turn Jeanette into a beauty contest winner, but Brittany was probably the only one who could make Jeanette look this wonderful while allowing her outfit to reflect her own personality. If Simon had to sum up the way the Jeanette looked today in three words, those three words would have been 'quiet, intelligent beauty'.

"Does it look, alright?" she asked nervously. "I hope it's not too gaudy."

"No, not at all," answered Simon quickly.

"Really," Jeanette replied, her features glowing with a look of relief from Simon's approval.

"Yea," he said shakily. "You're...you're..."

Simon was so nervous, he was losing words. His thoughts were running circles around his head. Over the wire he could hear, Alvin yelling to him to compliment her appearance. He looked around trying to find something to compare Jeanette prettiness to, a flower, a bird, anything. In the whirlwind of noises, sights and thoughts, Simon blurted what he would have considered the most random and probably stupidest thing he said in his life.

"You're...you're as pretty as a Belted Kingfisher," he said as he pointed to the kingfisher he had been watching earlier.

"I...look like...a kingfisher?" asked Jeanette, who was now a little confused on whether Simon's odd statement was compliment or not.

Behind the bushes, Alvin slapped his forehead in disbelief. _'A Kingfisher?_' he thought to himself. _'She looks like a Kingfisher? What kind of girl wants to know she looks like a Kingfisher?'_

"Yea, the blue band on its chest, the splendid blue wings," Simon explained awkwardly. "It's absolutely beautiful."

"So...that was...a compliment, right?" asked Jeanette, who was still a little confused.

"Of course," said Simon with a nervous smile. "The Belted Kingfisher is actually my favourite bird."

"Oh," exclaimed Jeanette, as a new flush of pink spread across her face. "Well, thank you for the compliment, Simon."

"It's too early to go to the aquarium, Simon," whispered Alvin over the wire. "Take her to the park for a while, get some sandwiches. We're going through with Operation Caterpillar."

In truth, Simon had hoped that Alvin would just leave him alone. It had been a while since he had hanged out with Jeanette and Alvin and Theodore's presence felt rather intrusive. However, he followed his brother's suggestion and asked Jeanette if she wanted to have something to eat before they went to the aquarium. Jeanette agreed and the couple made their way to the park.

"Jeanette's looking very pretty today," Theodore said to Alvin, once they were out of earshot. "She must have really been excited about this date."

Theodore's hope of pointing out the obvious was that Alvin might realize Jeanette's feelings about Simon and hopefully convince his older brother to call off this plan. But Theodore's comment simply reminded Alvin of Brittany because he knew that Brittany was the only one who could have dolled up Jeanette that well. As the two Chipmunks quietly stalked Simon and Jeanette to the park, Alvin whispered to his little brother.

"Keep an eye out, Theodore," he said a while later. "I have a feeling that Brittany and Eleanor maybe around."

"How do you know?"

"Brittany obviously helped Jeanette with her outfit," he answered. "I wouldn't be too surprised if we bumped into them."

Upon arriving at the park, Alvin found Simon and Jeanette seated on a bench under a tree having some sandwiches. Alvin smiled to himself, everything was going perfectly.

"Alright, Theodore, we're going to start Operation Caterpillar. Now start looking for caterpillars."

"I don't like caterpillars," whimpered Theodore. "They're round and they're furry."

"You're round and you're furry but you don't see me complaining, do you?" teased Alvin.

"Very funny, Alvin," replied Theodore as he looked through some bushes. "Why do we need a caterpillar anyway?

"Because girls are scarred of caterpillars and bugs," answered Alvin. "All we have to do is put a caterpillar on Jeanette's shoulder and she'll scream. That's where Simon comes in and saves the day."

"I don't know, Alvin..." trailed Theodore doubtfully.

"I've found one," Alvin announced happily as he held up a caterpillar. "Now let's get started."

Stealthily, the two Chipmunks approached the bench where Simon and Jeanette were seated. The two of them were engaged in conversation, something about the microorganisms in yeast used to bake bread. Leave it to Simon to find science even in food, Alvin thought to himself. Slowly and quietly, he placed the caterpillar on Jeanette's shoulder then returned to his hiding place in the bushes. It took a while but then Jeanette felt something crawling on her neck. Upon picking it up, she let out cry, which pleased Alvin for his plan was going well. However, what happened next was definitely not according plan.

"Simon, look! It's a Monarch Butterfly caterpillar!" Jeanette said suddenly.

"Why, so it is," said Simon as he looked at the caterpillar that Jeanette held in her hands.

Alvin's jaw had dropped to the floor after witnessing that reaction. Jeanette wasn't afraid of the caterpillar at all.

"It's odd that this little guy is so far away from any milkweed plants," Jeanette mentioned. "These caterpillars usually feed on those."

"I think I saw some purple milkweed on our way here," said Simon in response. "Let's drop him off there."

When they had moved a distance away, Alvin, in his frustration, started hitting his head on the tree next to the bench, muttering the word stupid every time his head hit the trunk. Theodore would have probably said something about Alvin's newfound self destructive tendencies but was cut short when he heard the sound of a branch breaking, followed by a scream and the sudden weight of chubby little Chipette falling on top of him from the tree above. Another scream followed and another Chipette fell, landing on a surprised Alvin to cushion her fall.

"Theodore!" called Eleanor when she realised that she had landed on him. "Are you alright?"

"Oww...I've had better landings," said Brittany.

"Get off me, Brittany," yelled Alvin impatiently. "What did you eat for breakfast anyway? Cement?"

Brittany was just about to give Alvin a piece of her mind but Eleanor held her back. Just then, they heard Simon's voice from across the wire.

"Alvin, come in," Simon said. "I heard a crash. Are you alright?"

"Yeah, I'm fine," said Alvin nervously as Brittany looked at him with a satisfied smirk. "I'll get back to you later."

Brittany turned to Eleanor and pointed to Alvin. "What did I tell you, Eleanor? They're all in this together. They're using this date with Jeanette to undermine my victory. Well, I'm going there right now and telling Jeanette all about this."

Theodore knew that if Jeanette thought that Simon was fooling her, it would seriously affect their relationship. In a desperate attempt he leapt and grabbed Brittany's leg and began to plead.

"Please, Brittany," he begged, "don't do that."

"Theodore, let go of my leg," she grunted as she tried to free herself from the chubby Chipmunk's grip.

Alvin, seeing an opening to fix this problem in his plans, quickly came up with an alibi as to why they were there and why they were using the wire.

"Listen, Brittany," he said as he attempted to explain his situation to the fiery Chipette. "There's a very good explanation for all this."

"Oh, really, Alvin," replied Brittany disbelievingly. "Let's hear it."

Alvin knew that Brittany was at the very end of her patience, so he knew from experience that the only way to wriggle his way out of this was to appeal to her good nature; a most difficult task for appealing to that part of Brittany always required considerable effort.

"Now I know this may sound strange but Simon really likes Jeanette, Brittany. But he's so bad at talking with girls he likes so he asked the two of us to help him with his date with Jeanette."

Brittany raised an eyebrow in disbelief, she was obviously unconvinced. Brittany was well aware of Alvin's tendency to sometimes omit and exaggerate certain facts so her suspicion of his motives was well founded. However, Alvin had a few tricks up his sleeve and the bouquet that they had sent the day before was going to be his ace in the hole.

"Do you remember the bouquet he sent Jeanette yesterday?" asked Alvin.

"Yes, I do."

"Well," continued Alvin deceitfully, "did you also know that Simon had sent a secret message in those flowers?"

"A secret message?" asked Brittany, who was now both a little confused and intrigued at the thought of a secret message hidden in the flowers.

"Yes, apparently flowers have meanings to them, 'the secret language of flowers', and the flowers he sent had this message hidden in them, 'innocent, modest, delicate beauty'. That is how important Jeanette is to Simon," answered Alvin with a cheeky grin.

"Really?" asked Eleanor in surprise. "Is that really what it means? That is so sweet of Simon."

"Yeah, Simon's not one for reading about the secret meanings of flowers but he did it so he could give Jeanette a very special bouquet," lied Alvin. "And that gesture alone speaks volumes."

By this time, Brittany was beginning to doubt herself; perhaps she had been too hasty in her accusations and should have given the Chipmunks the benefit of the doubt. Alvin, seeing Brittany doubt, knew that now was the time to drive his argument home.

"Besides, Brittany," he said, "didn't you help Jeanette get ready for her date. I can tell it's your work. I'm just helping my brother as you helped your sister."

Brittany let out a sigh of defeat, Alvin had a point there and it was one she couldn't refute.

"All right, Alvin," she said, "I'll give you guys the benefit of the doubt, but let's hurry. If Simon is as hopeless as you say he is then he's going to need all the help he can get."

As Brittany and Eleanor walked ahead to catch up with the unsuspecting couple, Theodore fell behind and whispered to Alvin.

"Alvin, I don't like this," he whispered. "I don't like lying to the Chipettes."

"Neither do I, Theodore," Alvin answered after a while, "but I have to win this election."

Chapter Three Ends

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Thanks for reading and once again, my apologies for the late update. As always, I look forward to hearing from so I can better myself to write better stories for you. Thanks.


	4. The Date: Part Two

Title: Chipmunk Politics

Written by: Somnion

Disclaimer: I do not own Alvin and the Chipmunks. They belong to Bagdasarian Productions.

So sorry for the late update. I've been real busy, not to mention I've had rewrite a lot of areas on this story so I could keep the Chipmunks and Chipettes in character. I hope I did alright. I'll update the story 'I do' as soon as I can. I already have a great idea for an Alvin and Brittany proposition for that one and I'll upload the story as soon as I can.

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Chapter 4: The Date: Part Two

Simon and Jeanette gazed in wonder as they walked through the many exhibits; fish and sea animals of all shapes, sizes and colour swam around them for the aquarium was built so that the exhibit tanks lined the walls and ceilings in order to give visitors the feeling as though they were walking under water with the fish swimming to their sides and above them. While the two bespectacled chipmunks admired the diversity of ocean fauna within the exhibits, their siblings followed behind. Given that the aquarium offered no place to hide, it was difficult to sneak too close so Alvin had been having trouble in giving Simon instructions.

"Geez, if only there were more places to hide. I can't get anywhere near them," Alvin murmured.

Alvin turned around and looked at his accomplices, who, by the way, were too busy watching the fish than to really bother about playing matchmakers for their middle siblings. It was irritating, to say the least, when you're the only one who's actually serious about a plan, especially when the plan is so critical that it could very well determine your victory in the school elections. Well, that's what Alvin thought at least.

"Will you three get your heads out of the water and back on earth where it belongs?" Alvin asked sarcastically. "We've got a mission here."

"Well, **somebody** obviously woke up on the wrong side of the bed this morning," Brittany remarked snidely, a little put-off with Alvin's behaviour.

"We can't get too close to them, Alvin," Theodore explained. "They'll see us if we do."

"So since we really can't do anything," Eleanor reasoned, "let's just take some time to enjoy the aquarium while we're here."

Alvin let out a defeated sigh; the three of them did have a point. He reached for his wire and started relaying a message to Simon.

"Alright, Simon, you're on your own from here," he said. "Just make sure you don't forget about Operation Dolphin."

"Alright," Simon whispered on the wire. "I'll remember."

Brittany, Eleanor and Theodore then looked to Alvin, the same question running through their minds. What was this 'Operation Dolphin'?

Simon looked at his watch and saw that the hands upon the face of the watch showed that it was half past two and he knew that he'd only have half an hour to put Alvin's plan into effect. He was pleasantly surprised that Alvin had decided to leave the two of them alone for a little while; it was becoming extremely bothersome with Alvin's voice constantly ringing in his ears all the time. Jeanette was busy watching the clownfish exhibit; it was a very nice exhibit complete with coral and anemones that gave the tank a very authentic look. Simon, however, was watching something else other than just the fish. Since Jeanette had shown up for their date, he found that he could barely keep his eyes of her. Her outfit suited her well and looked wonderful and her neat French braid was so different than the usual messy bun she always wore.

"Is something wrong, Simon?" asked Jeanette as she noticed Simon standing around not watching the fish.

"Oh, it's nothing," he replied. However, as soon as he said that he recalled that he still hadn't given her a proper compliment about her appearance; the kingfisher compliment was a close save but still wasn't a compliment. His head now in a better state than it was before; he found that he could actually mouth the right words this time around.

"I...I like what you did with your hair. It's very nice," he said, although with a bit of awkwardness in his voice.

"Oh, uh...umm...thank you," replied Jeanette shyly, her cheeks blushing pink from the sudden compliment. "Brittany did it for me. She said I would look nice in a French braid."

"You...you do," Simon responded bashfully.

There was a moment of silence between the two chipmunks. It was awkward but nice at the same time and neither of them could stop smiling, even though both of them were actually smiling at their feet given that neither of them could look the other in the eyes. During their silence, Simon thought deeply on the situation he was in. Alvin had set him up with a date with Jeanette simply as a means to win the election and he followed through with his brother's plan partially because he was blackmailed and also because he, despite their constant arguments, loved his brother and knew how much the victory would mean to him. However, after all that had happened, he found now that he couldn't bring himself to deceive Jeanette anymore. He looked to his watch; it was fifteen minutes till 'Operation Dolphin' was to take off. He felt his hand reach into his pocket, his fingers brushing against the tickets. Alvin would throw a fit if he didn't pull off the operation but Simon didn't want to deceive the green eyed Chipette he was dating any further. So he decided that he'd undergo 'Operation Dolphin', not for Alvin's sake but for Jeanette's, so that she'd have a good time and a memorable date.

"Come on, Jeanette," he said. "There's still one more place to go."

Jeanette wondered where or what this last attraction was going to be for Simon insisted on it being a surprise. It was a surprise indeed when they came to the counter and Simon produced two tickets for a new attraction called 'Dolphins up close'. The two of them then followed one of the dolphin trainers to a special area where they met four dolphins. The trainer then showed both Simon and Jeanette how the dolphins were fed and then handed over the food to the excited chipmunks and asked them to give it a try. Simon fed the dolphins, taking the time to pet the ones that came close yet he stayed close to Jeanette, making sure she watched her footing for he was aware of her clumsiness. However, no such accident happened and Jeanette thoroughly enjoyed the ten minutes they had with the dolphins, feeding them and petting them. They left the aquarium at three and Jeanette was beaming like sunshine as she had a blast at the aquarium.

"Thanks for the great time today, Simon," she said as they left the aquarium. "I had a lot of fun."

"It was no problem," he said nervously. "I mean...I had fun too."

Just when Simon had thought he was going to have another moment with Jeanette, Alvin's voice cracked across the wire, ruining any possibility of a tender moment between the two chipmunks.

"Okay, now we're going to bring this whole thing home, Simon," Alvin whispered over the wire. "Take Jeanette to the zoo. We're gonna put 'Operation Panda' into full gear."

Why Alvin would come up with such unoriginal names for his hair-brained schemes was beyond Simon. The oddly named 'Operation Panda' was basically just taking Jeanette to see the pandas at the zoo. Simon had by this time made up his mind that he wasn't going to deceive Jeanette any further and the logical Chipmunk was planning to tell his brother that he was not going to have any part of it and was about to go home but reconsidered, when he realised that Jeanette might be interested in seeing the pandas at the zoo. He asked her if she was interested and when she answered him with an enthusiastic 'yes', the couple made their way to the zoo, followed by their siblings who kept themselves hidden at all times. Alvin and Brittany were leading the way while Theodore and Eleanor lagged behind slowly. Theodore walked slowly, his mind a swirling whirlpool of regret, guilt and doubt. He knew what he was doing was wrong, Jeanette was their friend and deceiving her and her sisters would be a blow to the trust they shared amongst each other. Suddenly, Eleanor took his arm and held it, surprising the plump, little Chipmunk and pulling him away from his thoughts.

"I'm glad," she said when she saw Theodore turn his head to acknowledge her.

"Glad for what?" asked the confused Chipmunk nervously.

"Jeanette looks very happy," she answered. "She really does like Simon and it's thanks to both you and Alvin that Simon is actually out on a date with her. So, thank you for that, Theodore."

With that, while Alvin and Brittany were still looking away, Eleanor leaned up and placed a soft kiss on Theodore's chubby cheek, a sign of how grateful she was for her sister's happiness. Theodore gulped and gave Eleanor an awkward smile, blushing the entire time. As they walked hand in hand, Theodore realised that he wasn't going to go through with this crazy plan anymore. Eleanor trusted him and his brothers and he wasn't planning on breaking that trust any further. When he got the chance he'd wire Simon and tell him to call this plan off. Theodore knew that Simon would listen, he just knew he would.

They arrived at the zoo and found Simon and Jeanette buying tickets. Theodore knew that this was his chance. Taking his chance to slip away from the group, he got onto his wire and whispered his message.

"Simon, it's me, Theodore," he whispered softly. "We have to stop this. I...I don't want to lie to the Chipettes anymore."

"Don't worry, Theodore," assured Simon over the wire. "I'm not going through with Alvin's plan either."

"What'll we say to Alvin then?" asked Theodore nervously.

"I'll think of something. Trust me."

Simon thought hard. He wished he knew a way to get Alvin to see how wrong this deception was. 'Operation Panda' was the agreed operation where Simon was supposed to convince Jeanette into voting for Alvin and the blue-clad Chipmunk knew he was running out of time. Then it dawned on him and as he planned the scheme in his head, laying out all the details of the elaborate ruse in his mind, did he realise just how good he was at planning schemes, probably as good as Alvin. The plan was fool-proof. Quickly, he wired his younger brother.

"Alright, Theodore. I've got a plan."

"What is it?" asked Theodore.

"No time to explain," answered the bespectacled Chipmunk. "But I'll need you to do two things for me. First try to contact Louie and Michael and see if you can get them to come to the zoo, secondly, try to find the zookeeper. I'll stall Alvin as long as I can."

"Okay, I'll do my best."

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Chapter 4 Ends

Hope you guys enjoyed this. It's a little short but I hope it was alright. Besides, I always get worried that if I write too much, people might get bored and lose interest. Anyway, any reviews from readers will be greatly appreciated. Just press the little green button and type away...You know you want tooooo...


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